Hydrochloric Acid → (2,6-Dimethyl-3-nitrophenyl)methanol

HRID 1871103Notes

Reaction equation

HRID 1871103 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([CH3:14])[C:3]=1[C:4](O)=[O:5].Cl>O1CCCC1>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([CH3:14])[C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2393292,6-Dimethyl-3-nitrobenzoic acid

Product 1

HCID 10487641(2,6-Dimethyl-3-nitrophenyl)methanolYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-dimethyl-3-nitrobenzoic acid (3.09 g) in tetrahydrofuran (5 ml) was added borane-methyl sulfide complex (2.41 g) under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature, for 1 hour at ambient temperature, and then for 4 hours under heating. To the mixture was added 1N hydrochloric acid under ice-cooling, and the mixture was allowed to stand overnight. The mixture was extracted with ethyl acetate twice, and the combined organic layer was washed with saturated sodium bicarbonate solution, water and brine, dried over magnesium sulfate and concentrated. The residue was recrystallized with diisopropyl ether to give 2,6-dimethyl-3-nitrobenzyl alcohol (2.296 g) as a pale yellow crystal.

Workup

  1. temperaturecooling
  2. temperaturefor 4 hours under heating
  3. temperaturecooling
  4. waitto stand overnight
  5. extractionThe mixture was extracted with ethyl acetate twice
  6. washthe combined organic layer was washed with saturated sodium bicarbonate solution, water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was recrystallized with diisopropyl ether

Sources & evidence

ORD record
ord-05d0e1f45ed2449aa32f189a88d42739
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

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